Ethyl 2-formylbutanoate → HCID 178437179, compound

Reaction equation

[Na].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([NH2:14])=[NH:13])=[CH:6][CH:5]=1.[CH:15]([CH:17]([CH2:23][CH3:24])[C:18](OCC)=O)=[O:16]>C(O)C>[CH2:23]([C:17]1[C:15](=[O:16])[N:13]=[C:12]([CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[NH:14][CH:18]=1)[CH3:24]

Participants

Procedure

Sodium (0.23 g) in dry ethanol (10 ml) was treated with 3-(4-fluorophenyl)propionamidine hydrochloride (Int. A108) (1.02 g). Ethyl 2-formylbutyrate (0.72 g) was added and the mixture refluxed for 6 h then maintained at room temperature for a further 24 h. The reaction mixture was concentrated in vacuo, and the residue treated with water and acidified with conc. hydrochloric acid. The white precipitate was filtered off, washed with water and dried in vacuo at 40° C. overnight, to give the title compound, (982 mgs, 80%) 1H-NMR (CDCl3) δ 1.22 (3H, t), 2.52 (2H, q), 2.94 (2H, m), 3.09 (2H, m), 6.96 (2H, m), 7.24 (2H, m), 7.84 (1H, s) and 13.06 (1H, br. s). (APCI+) Found (M+1)=247, C14H15FN2O requires 246.